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Herbie's Hideaway

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Shell Cottage

4 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Come and enjoy a delightful vacation at "Shell Cottage"! Located on the popular East Side of Chincoteague Island, you'll enjoy water views of the Assateague Channel and lounging on the outside decks (one which includes an outside shower). This open floor plan home features two bedrooms downstairs (both with a queen bed and a TV each), a half bathroom, and spacious living room & kitchen. Upstairs you'll find 2 more bedrooms (one with twin trundle and the other with 2 twins) and a full bathroom. Just a short drive to the Memorial Waterfront Park, public boat launch, downtown area and restaurants! Shell Cottage also includes all the modern conveniences such as wireless internet, washer/dryer, dishwasher and more. And you'll have room to park your boat and trailer. This just may be your perfect vacation spot!

IMPORTANT NOTE: The hot tub is OPEN as of April 16, 2026.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Lighthouse

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Boat Dock
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Nestled in the picturesque Captain's Cove community, this exquisite three-bedroom, two-bathroom waterfront residence represents the pinnacle of sophisticated coastal living. The stunning new construction boasts an airy, well-conceived open floor plan that seamlessly blends indoor refinement with the serene beauty of unobstructed bay views.

The chef's kitchen stands as a culinary sanctuary, where premium finishes and state-of-the-art appliances await the discerning home cook. In the evening hours, the ambient glow of the fireplace creates an atmosphere of unparalleled comfort and tranquility. For entertainment aficionados, each bedroom features a Smart TV—including the primary bedroom suite.

Perhaps most alluring is the property's 4-season room and direct bulkhead access to the bay, with boat dockage available for nautical enthusiasts. One might say this home doesn't just offer a lifestyle—it launches one.

The distinguished community amenities elevate everyday living to resort-quality experiences, featuring both indoor and outdoor swimming pools, a fitness facility, and an on-site restaurant. The adjacent marina and golf course create a playground for those with a passion for waterfront and fairway pursuits.

This exceptional property affords the advantage of being merely 20 minutes from the wild horses and pristine shores of Chincoteague Island, with the Assateague Island National Seashore's and beach just beyond. For those seeking more vibrant diversions, Ocean City's renowned boardwalk and attractions await just 30 minutes away, while Maui Jack's Waterpark offers family entertainment nearby. As one of Coastal Shore's newest offerings, don't sleep on this one. It will book quickly!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- No pets are permitted on the premises.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Shady Side

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the other has a queen bed. There is also a full bath on the second floor. The loft features a futon with a full mattress. The large back porch is equipped with a gas grill and picnic table for your cookouts and crab feasts! 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Robert's Retreat

5 Bedrooms
3 Baths & 1 Half
10 Guests
Captain's Cove
Water View
Gas Grill
Pool
Internet

Discover the ultimate family retreat in this brand new 5-bedroom, 3.5-bathroom home located in the picturesque Captain's Cove Community, boasting over 2,500 square feet of luxurious living space. With breathtaking natural marshland and water views, this residence is perfect for wildlife watching and enjoying serene sunsets from expansive decks designed for outdoor dining and recreation. The upgraded kitchen and all-new furnishings create an inviting atmosphere for making cherished memories with loved ones. Take advantage of community amenities including indoor and outdoor pools, a 9-hole golf course, fitness room, waterfront restaurant, boat ramp, and fishing pier to ensure endless fun-filled days. Don’t miss out on this exceptional opportunity to create lasting family traditions in a relaxing vacation paradise!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property does not allow pets. 

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Sandy Penny

3 Bedrooms
3 Baths
14 Guests
Chincoteague Island
Water View
Screened Porch
Internet

Experience elevated coastal living at 'Sandy Penny', a stunning, brand-new vacation home tucked along peaceful Clarkson Lane with beautiful, snipet water views of the Assateague Channel. Thoughtfully designed with comfort and sophistication in mind, this home is the perfect retreat for families, couples, and friends seeking a luxurious Chincoteague Island getaway.

From the moment you step inside, you’ll notice the premium furnishings, designer finishes, and upscale appliances that set 'Sandy Penny' apart. The bright, open-concept living area features expansive windows that allow natural lighting, and space for gathering or entertaining. Whether you're savoring your morning coffee or winding down after a day of exploring, this space makes every moment feel special.

The chef’s kitchen is fully equipped with top-of-the-line appliances, custom cabinetry, and elegant stone countertops, making it a joy to cook and gather. Enjoy meals indoors or take advantage of the outdoor spaces to dine with soft bay breezes and glimpses of passing wildlife.

Sandy Penny offers three beautifully appointed bedrooms, each with its own private en-suite bathroom, providing exceptional comfort and privacy for every guest. Luxurious bedding, spa-inspired bathrooms, and serene décor ensure a restful experience from start to finish.

Located in one of the island’s most desirable areas, you’ll be just minutes from: Assateague National Seashore and the world-famous wild ponies; downtown Chincoteague’s shops, ice cream parlors, and restaurants; kayaking, boating, and fishing along the Assateague Channel; scenic trails and bike paths and more!

Whether you’re seeking serenity, adventure, or a little of both, Sandy Penny delivers a refined coastal escape with all the comforts of a luxury home. Book your stay today and experience Chincoteague Island from a place where every detail is designed for relaxation and unforgettable memories.

Bed Configuration: Downstairs Bedroom - King bed; Upstairs Bedroom 1 - King bed; Upstairs Bedroom 2 - Triple Bunk Bed & Twin-over-Full Bunk with pull-out Twin Trundle; Living Room - Queen Sleeper Sofa; Additional Rollaway Twin Bed

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Crabby Baker

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet
Outdoor Shower

Welcome to a waterfront townhome retreat that delivers island living with a front-row view of the lighthouse and sunrises that will surely outshine your alarm clock. Set in one of Chincoteague Island’s most desired areas, this pet-friendly 2-bedroom, 2.5-bath home pairs comfort, charm, and a little vacation energy in all the right ways.

Inside, the layout offers easy everyday living and inviting spaces to unwind after a day on the water or at the beach. The living room is anchored by a 75-inch television, perfect for movie nights, game days, or simply pretending you are “just resting your eyes.” Upstairs, the primary bedroom features a private bathroom and a waterside balcony, creating a peaceful retreat for morning coffee, evening breezes, and uninterrupted water views. A second bedroom and additional baths provide flexibility for guests, work-from-home needs, or both. The extra half bath adds convenience for entertaining, while the townhouse design keeps daily vacationing practical and fun. 

Outdoor living is just as appealing, with a fishing and crabbing pier that invites relaxed afternoons and fresh catches, plus a hot and cold outside shower for easy cleanup after beach trips. Imagine casting a line at dusk, then rinsing off before dinner as the water glows around you. You are also conveniently close to Maui Jack’s Waterpark and Assateague Beach, so fun is never far from home.

If you have been searching for a vacation spot that feels equal parts coastal escape and everyday comfort, this one checks all the boxes. Book today and see why this waterfront townhouse is easy to love.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with a pet fee of $150 - one dog max. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Sunset Bay Villa 312

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pool
Internet

Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are TVs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! | Note: This villa has access to a 14' boat slip.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Vast Views

2 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Pool
Internet

Welcome to your perfect coastal getaway in charming Chincoteague Island! This newly remodeled townhouse offers the ideal blend of comfort and modern amenities, featuring two cozy bedrooms and three full bathrooms as well as an open floor plan perfect for entertaining! Step into a space where everything sparkles with newness, from the stylish fixtures to the thoughtfully placed flat-screen TVs in every room. The innovative touches, such as bathrooms equipped with cutting-edge built-in Bluetooth speakers, make this home perfect for both relaxation and entertainment.

The location couldn't be better for beach lovers and adventure seekers. Step outside to enjoy exclusive community amenities like a swimming pool and a pier with direct water access to Assateague Channel. Try your hand at fishing or crabbing, or tie up your boat - there’s no better way to end your day than with mesmerizing water and lighthouse views right from your vacation home! The community pool provides a refreshing escape on warm summer days, while the nearby Memorial Park offers tennis courts and a playground for your enjoyment.

The East Side location could not be more ideal - when you're not in the mood to cook, local restaurants are just a short stroll away, serving up fresh seafood and coastal favorites. The area's attractions are sure to keep you entertained, with Maui Jack's Waterpark and the pristine Assateague Beach both within easy reach. Nature lovers can explore the famous wild ponies and abundant wildlife that make this island so special.

This townhouse isn't just a rental – it's your piece of paradise that offers the laid-back coastal lifestyle that Chincoteague is famous for. Whether you're seeking a peaceful retreat or an adventurous beach vacation, this home delivers the best of both worlds.

This pet-friendly home also offers the option to rent neighboring units, making it ideal for larger groups or family gatherings! Make this brand new townhouse your sanctuary on Chincoteague Island, embracing a blend of comfort, convenience, and natural beauty all around. Your island lifestyle awaits!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Pearl

4 Bedrooms
3 Baths & 1 Half
8 Guests
Cape Charles
Water View
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Welcome to "The Pearl" - and your next chapter of coastal living in the sought-after Bay Creek community on Virginia's Eastern Shore. This brand new four-bedroom, three-and-a-half-bathroom home is a stunning retreat where modern elegance meets small-town charm, and every detail has been thoughtfully curated for refined living.

Step inside to discover a light, bright, and airy interior that immediately puts you at ease. Professionally decorated from top to bottom, the home showcases a sophisticated aesthetic that blends coastal warmth with contemporary flair. The upscale kitchen serves as the heart of the home, outfitted with premium finishes and designed to inspire both casual meals and memorable gatherings. Generous living spaces flow seamlessly throughout, while serene pond views from the home create a tranquil backdrop you will never tire of admiring.

The spacious primary bedroom offers a private sanctuary, complemented by three additional well-appointed bedrooms that provide ample room for family and guests alike. With three and a half beautifully finished bathrooms, morning routines remain effortless no matter how full the house may be.

Beyond the front door, the Bay Creek community elevates everyday life into something truly extraordinary. Guests enjoy access to world-famous golf courses, resort-style pools, a state-of-the-art fitness and life center, scenic walking trails, and an on-site restaurant. Just a short distance away, the beloved Cape Charles Beachfront awaits with its golden sands and breathtaking Chesapeake Bay sunsets. Stroll through the charming town to explore Central Park, local boutiques, and a vibrant dining scene. Convenient grocery shopping at nearby Food Lion ensures daily errands are a breeze, while the iconic Chesapeake Bay Bridge-Tunnel connects you effortlessly to the greater Hampton Roads region.

This is more than a rental — it is a lifestyle. Book your vacation and experience the best of Eastern Shore living for yourself.

SPECIAL NOTES:

This rental home is NO SMOKING and NO PETS.

Linens and towels are included with your reservation.

Usage of the Bay Creek Resort Amenities requires an additional fee of $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge with billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddleboarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Blissful Oasis

3 Bedrooms
2 Baths
8 Guests
Waterfront
Boat Dock
Gas Grill
Internet

Picture yourself sipping morning coffee on the water's edge, watching herons wade along the shoreline while the Chesapeake Bay stretches endlessly before you. This stunning waterfront rental delivers the kind of coastal living most people only dream about. Tucked away in a beautifully secluded mid-shore location, this three-bedroom, two-bathroom home offers a rare combination of peaceful seclusion and everyday convenience. The star of the show? A long private pier that extends into the bay, practically begging you to launch a kayak, or simply sit at the end with a fishing rod and zero responsibilities.

Inside, the home has been thoughtfully updated to match the magnificence of its surroundings. The renovated kitchen features brand new appliances and a fresh, modern feel that makes meal prep genuinely enjoyable — whether you're cooking up the catch of the day or just reheating leftovers without judgment. Both bathrooms have been completely redone, offering crisp, clean finishes that feel wonderfully indulgent after a long day on the water. The three bedrooms provide comfortable retreats, with the primary bedroom serving as your personal sanctuary overlooking the bay. Natural light pours through the home, connecting every room to the breathtaking waterfront scenery outside.

Despite the gloriously remote feel, practical amenities remain within easy reach. Grocery shopping at Food Lion is a short drive away, and the iconic Chesapeake Bay Bridge-Tunnel provides a scenic connection to the broader Hampton Roads region whenever adventure calls.

This is a home where the rhythm of the tides replaces the noise of daily life. Waterfront rentals like this book quickly - reserve your dates and experience a vacation full of lasting memories!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

The Blue Pearl

4 Bedrooms
3 Baths & 1 Half
10 Guests
Cape Charles
Waterfront
Gas Grill
Screened Porch
Pool
Internet

Welcome to your dream waterfront home at Bay Creek Resort in beautiful Cape Charles, VA! This stunning 4-bedroom, 3.5-bathroom luxury retreat boasts direct beach access and breathtaking sunset views over the bay. Enjoy the open floor plan downstairs - perfect for entertaining or just enjoying your own space. The expansive decks lend themselves to comfortable outdoor lounging or dining al fresco. Upstairs you'll bask in the spaciousness of the two primary bedroom suites—one is beachfront and features a king bed and jacuzzi tub, and the other has a king bed and private sitting area—perfect for adults seeking comfort and relaxation. The two-level all-season rooms with floor-to-ceiling windows invite you to soak in the natural beauty and wildlife that surround you. The world-class community amenities complete the 5-star package -  professionally designed golf course, fine dining, expansive fitness room, pools with water slides, and golf cart trails - and they all enhance your vacation experience. Make unforgettable memories in this luxurious beachfront paradise where every day feels like a getaway!

SPECIAL NOTES:

This rental home is NO SMOKING and NO PETS.

Linens and towels are included with your reservation.

Usage of the Bay Creek Resort amenities is an additional $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge with billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddleboarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

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